Patent GB-325550-A (GB)
Title: Improvements in the manufacture and production of nitrogenous vat dyestuffs
IPC: C09B6/00
Filed: 1928-10-15
Abstract: 325,550. Johnson, J. Y., (I. G. Farbenindustrie Akt.-Ges.). Oct. 15, 1928. Divided on and addition to 318,18,0. Samples furnished. Vat dyes are made by condensing polynuclear heterocyclic compounds containing a plurality of negative substituents of identical or different character, such as halogen or nitro groups, simultaneously or successively with a plurality of cyclic nitrogenous compounds containing at least one reactive hydrogen atom attached to a nitrogen atom, at least one of the cyclic nitrogenous compounds containing a system of four or more condensed rings and at least one of the components taking part in the reaction being vatable. The condensation may be effected in a solvent or diluent, such as nitrobenzene, nitrotoluene, nitronaphthalene, or naphthalene, and in the presence of a condensing catalyst, such as copper, aluminium or mercury compounds thereof. As heterocyclic and cyclic compounds those derived from indigo, thioindigo, anthraquinoneazines, flavanthrone, anthraquinoneacridones, carbazoles, quinolines, pyrazolanthrones, naphthazines, benzene, naphthalene, anthracene, phenanthrene, perylene, pyrene, the various dianthrones connected with each other by one or more ring systems, dibenzanthrone, isodibenzanthrone, dibenzpyrenequinones and anthanthrones are specified. As in the case of the parent Specification, the components need not be brought into reaction in exact stoichiometric proportions. In examples, (1) monochlormonobromanthraquinonebenzacridone (made by condensing 1-amino-2-sulpho-4- bromanthraquinone with 3-chlor-6-aminobenzoic acid, effecting ring closure to the acridone by means of chlorsulphonic acid, the sulpho group being thereby split off, and finally replacing the amino group by bromine by way of the diazo compound) is condensed with aminodibenzanthrone (Specification 1818/05, example 3) and 1-aminoanthraquinone, the product dyes cotton in very fast grey shades. (2) The dichlor derivative obtained by chlorinating in chlorsulphonic acid, with iodine as catalyst, the product obtained by alkali fusion and subsequent ethylation of pyrazolanthrone, is condensed with 1-aminoanthraquinone and aminodibenzanthrone (obtained by reducing the product obtained by nitrating dibenzanthrone in nitrobenzene); the product dyes in red violet shades. (3) Dibrom-6 : 6<1>-dichlor-4 : 4<1>-dimethylthioindigo, obtained by brominating 6 : 6<1>-dichlor- 4 : 4<1>-dimethylthioindigo in nitrobenzene, is condensed with the aminodibenzanthrone of example 2 and 1-aminoanthraquinone (green-grey to black). (4) Dibromflavanthrone, obtained by brominating flavanthrone in chlorsulphonic acid, is condensed with aminodibenzanthrone and 1-aminoanthraquinone (olive grey) or with aminodibenzanthrone and cyclohexylamine (olive). (5) 2 : 3<1>-Dibrom- N - dihydro - 1 : 2 : 2<1> : 1<1> anthraquinoneazine is condensed with 1-aminoanthraquinone and 5- amino - 4' - benzoylamino - 8 - methoxy 1 : 1<1>- anthrimidocarbazol (dark brown). (6) Trichloranthraquinonebenzacridone (by chlorinating in an organic solvent with chlorine or sulphuryl chloride) is condensed with aminodibenzanthrone, 1-aminoanthraquinone, and 1: 5-diaminoanthraquinone (grey to black), or with 1-aminoanthraquinone and 1-amino-5-benzoylamino-8-methoxyanthraquinone (grey). (7) Tribromanthraquinonenaphthacridone (by brominating in chlorsulphonic acid the anthraquinonenaphthacridone obtained by condensing 1-chloranthraquinone-2-carboxylic acid with 2-naphthylamine and closing the ring) is condensed with 1-amino-4-methoxyanthraquinone and monoaminopyranthrone (made by nitrating pyranthrone in nitrobenzene and reducing) (grey). (8) Tribrom-N-dihydro-1 : 2 : 2<1> : 1<1>- anthraquinoneazin (by brominating in chlorsulphonic acid) is condensed with 1-aminoanthraquinone and 1-amino-4-methoxyanthraquinone (grey), or with 1-aminoanthraquinone and aminodibenzanthrone (green grey to black). (9) Hexabrom - 8 : 8<1> - dioxy-2 : 1 : 1<1> : 2'-naphthazine (bv brominating the naphthazine) is condensed with aminodibenzanthrone and 1-aminoanthraquinone (green grey). (10) Octochlor-8 : 8<1>-dioxy-2 : 1 : 1<1> : 2<1>-naphthazine (by chlorinating in nitrobenzene) is condensed with 1-aminoanthraquinone and aminodibenzanthrone (green-grey to black).